Dimethylformamide → 2,2-Dimethyl-4(5-methyl-thien-2-yl)-chrom-3-en-6-al

HRID 2620

Reaktionsgleichung

Reaktionsgleichung von HRID 2620
[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[O:3]1.[Li]C(C)(C)C.CN([CH:28]=[O:29])C>C1COCC1.CCCCC.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:19])[CH:11]=[C:10]([C:12]2[S:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:28]=[O:29])[CH:8]=2)[O:3]1

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 861915082,2-Dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene2×HCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 1317205762,2-Dimethyl-4(5-methyl-thien-2-yl)-chrom-3-en-6-al

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8003PentaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a cold (-78° C.) solution of 2,2-dimethyl-4(5-methyl-thien-2-yl)-6-bromo-chrom-3-ene (Compound R, 1.2 g, 3.6 mmol) in THF (10 mL), was added t-BuLi in pentane (1.7M solution, 2.3 mL). After 30 minutes, DMF (465 mg, 5 mmol) was added and the mixture was allowed to warm to ambient temperature and stirred for 3 hours. The mixture was diluted with ethyl acetate (150 mL), washed with brine (10 mL), dried and the solvent was removed by evaporation. Purification by chromatography on silica gel column gave the title compound as a colorless oil.

Aufarbeitung

  1. washwashed with brine (10 mL)
  2. customdried
  3. customthe solvent was removed by evaporation
  4. customPurification by chromatography on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-9f2a11bfe87a4bf99972d2587a25f59f
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728846

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